Nitrogen-containing compound, and electronic element and electronic device using same

ABSTRACT

The present application relates to a nitrogen-containing compound. The structural formula of the nitrogen-containing compound is as shown in a Formula 1, in which a ring A and a ring B are each independently selected from a benzene ring or a fused aromatic ring with 10 to 14 ring-forming carbon atoms, and at least one of the ring A and the ring B is selected from the fused aromatic ring with 10 to 14 ring-forming carbon atoms; L is selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group with 3 to 30 carbon atoms; and Het is a substituted or unsubstituted nitrogen-containing heteroaryl group with 3 to 30 carbon atoms. The nitrogen-containing compound of the present application can improve the luminous efficiency of an organic electroluminescent device and the conversion efficiency of a photoelectric conversion device using the nitrogen-containing compound.

CROSS REFERENCE TO RELATED APPLICATIONS

The application claims the priority of the Chinese patent applicationNo. 202010383441.X filed on May 8, 2020 and the priority of the Chinesepatent application No. 202010732484.4 filed on Jul. 27, 2020, and thecontents of the Chinese patent applications are hereby incorporated byreference in their entirety as a part of the application.

TECHNICAL FIELD

The application belongs to the technical field of organic materials, andparticularly provides a nitrogen-containing compound, and an electronicelement and an electronic device using the same.

BACKGROUND

An organic light-emitting element is a representative example of anorganic electronic element. Generally speaking, an organiclight-emitting phenomenon refers to a phenomenon that electric energy isconverted into light energy by using organic substances. An organiclight-emitting element using the organic light-emitting phenomenon isgenerally provided with a structure including an anode and a cathode,and an organic layer positioned therebetween. In order to improve theefficiency and the stability of the organic light-emitting element, theorganic layer is usually formed by a multi-layer structure formed bydifferent substances, for example, the organic layer can be formed by ahole injection layer, a hole transport layer, a light-emitting layer, anelectron transport layer, an electron injection layer and the like. Forthe structure of such organic light-emitting element, if a voltage isapplied between the two electrodes, holes are injected into the organiclayer from the anode, electrons are injected into the organic layer fromthe cathode, when the injected holes and electrons meet each other,excitons are formed, and when the excitons undergo transition to aground state again, light is emitted.

Generally speaking, electron transport materials are compounds withelectron-deficient nitrogen-containing heterocyclic groups, and most ofthe electron transport materials have relatively high electron affinity,so that the electron transport materials have relatively high electronaccepting capability, but compared with hole transport materials, theelectron mobility of common electron transport materials such asaluminum 8-hydroxyquinolinate is far lower than the hole mobility of thehole transport materials, so that in an OLED device, on one hand, therecombination probability of holes and electrons caused by unbalancedinjection and transport of carriers is reduced, and the luminousefficiency of the device is reduced; and on the other hand, the electrontransport materials with lower electron mobility can cause the workingvoltage of the device to rise, so that the power efficiency isinfluenced, which is unfavorable for the energy conservation.

SUMMARY

Aiming at the problems in the prior art, the aims of the presentdisclosure to provide a nitrogen-containing compound, and an electronicelement and an electronic device using the same. The nitrogen-containingcompound can be used as a hole blocking layer and/or an electrontransport layer of an organic electroluminescent device.

In a first aspect, the present disclosure provides a nitrogen-containingcompound, having a structural formula as shown in Formula 1:

where ring A and ring B are the same or different, and are eachindependently selected from a benzene ring or a fused aromatic ring with10 to 14 ring-forming carbon atoms, and at least one of the ring A andthe ring B is the fused aromatic ring with 10 to 14 ring-forming carbonatoms;

L is selected from a single bond, substituted or unsubstituted arylenewith 6 to 30 carbon atoms, and substituted or unsubstitutedheteroarylene with 3 to 30 carbon atoms;

each Q¹ and each Q² are the same or different, and are eachindependently selected from deuterium, halogen group, cyano, haloalkylwith 1 to 10 carbon atoms, alkyl with 1 to 10 carbon atoms, cycloalkylwith 3 to 15 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthiowith 1 to 4 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms,triarylsilyl with 18 to 24 carbon atoms, aryl with 6 to 12 carbon atoms,aralkyl with 7 to 13 carbon atoms, heteroaryl with 4 to 12 carbon atoms,and heteroaralkyl with 5 to 13 carbon atoms;

n represents the number of Q¹, which is selected from 0; and mrepresents the number of Q², which is selected from 0 or 1;

Het is substituted or unsubstituted nitrogen-containing heteroaryl with3 to 30 carbon atoms;

Ar₁ and Ar₂ are the same or different, and are each independentlyselected from hydrogen, substituted or unsubstituted alkyl with 1 to 20carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbonatoms, and substituted or unsubstituted heteroaryl with 3 to 30 carbonatoms;

the substituents in L, Het, Ar₁ and Ar₂ are the same or different, andare each independently selected from deuterium, halogen group, cyano,aryl with 6 to 25 carbon atoms, heteroaryl with 3 to 25 carbon atoms,alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms,cycloalkyl with 3 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms,alkylthio with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbonatoms, and triarylsilyl with 18 to 24 carbon atoms.

In a second aspect, the present disclosure provides an electronicelement, comprising an anode, a cathode which are arranged oppositely tothe anode, and a functional layer arranged between the anode and thecathode, and the functional layer contains the nitrogen-containingcompound in the first aspect of the present disclosure; preferably, thefunctional layer comprises an electron transport layer, and the electrontransport layer contains the nitrogen-containing compound; andpreferably, the functional layer comprises a hole blocking layer, andthe hole blocking layer contains the nitrogen-containing compound.

In a third aspect, the present disclosure provides an electronic device,comprising the electronic element in the second aspect of the presentdisclosure.

Through the above technical solution, the nitrogen-containing compoundprovided by the present disclosure has a molecular structure in whichheteroaryl is bonded to fused-ring adamantane fluorene. On one hand, themolecular structure can reduce an energy level injection barrier, sothat the working voltage of an organic electroluminescent device isreduced, and the open-circuit voltage of a photoelectric conversiondevice is improved. On the other hand, the molecular structure has largemolecular weight, and a fused ring structure can increase sterichindrance, so that the structure is adjusted, the material is difficultto crystallize or aggregate, and the material has longer service life inthe electronic element. Not only that, the molecular structure haselectron-rich characteristics, the polarity of the whole molecule isenhanced, and directional arrangement of material molecules is morefacilitated, so that injection and transport of electrons are enhanced,the electron conductivity of an electron transport material is enhanced,and meanwhile, the luminous efficiency of an organic electroluminescentdevice using the nitrogen-containing compound can be improved; and theconversion efficiency of the photoelectric conversion device using thenitrogen-containing compound is improved.

Other features and advantages of the present disclosure will bedescribed in detail in the subsequent specific embodiments.

BRIEF DESCRIPTION OF THE DRAWINGS

The drawings are used to provide a further understanding of the presentdisclosure and constitute a part of the description, and are used toexplain the present disclosure together with the following specificembodiments, but do not constitute limitations on the presentdisclosure. In the drawings,

FIG. 1 is a structural schematic diagram of an organicelectroluminescent device according to an embodiment of the presentdisclosure.

FIG. 2 is a structural schematic diagram of a first electronic deviceaccording to an embodiment of the present disclosure.

FIG. 3 is a structural schematic diagram of a photoelectric conversiondevice according to an embodiment of the present disclosure.

FIG. 4 is a structural schematic diagram of a second electronic deviceaccording to an embodiment of the present disclosure.

DESCRIPTION OF REFERENCE SIGNS

100, anode; 200, cathode; 300, functional layer; 310, hole injectionlayer; 321, hole transport layer; 322, electron blocking layer; 330,organic light-emitting layer; 341, hole blocking layer, 340, electrontransport layer; 350, electron injection layer; 360, photoelectricconversion layer; 400, first electronic device; and 500, secondelectronic device.

DETAILED DESCRIPTION

The specific embodiments of the present disclosure are described indetail below in combination with the drawings. It should be understoodthat the specific embodiments described herein are only used toillustrate and interpret the present disclosure, but not to limit thepresent disclosure.

In a first aspect, the present disclosure provides a nitrogen-containingcompound, having a structural formula as shown in Formula 1:

where ring A and ring B are the same or different, and are eachindependently selected from a benzene ring or a fused aromatic ring with10 to 14 ring-forming carbon atoms, and at least one of the ring A andthe ring B is the fused aromatic ring with 10 to 14 ring-forming carbonatoms;

L is connected with the ring A or the ring B;

specifically, in the present disclosure, the nitrogen-containingcompound as shown in the Formula 1 can be selected from the compound asshown in Formula A or Formula B;

when the ring A or the ring B is provided with substituent group Q¹ orQ², L is only connected with the ring A itself or with the ring Bitself.

L is selected from a single bond, substituted or unsubstituted arylenewith 6 to 30 carbon atoms, and substituted or unsubstitutedheteroarylene with 3 to 30 carbon atoms;

each Q¹ and each Q² are the same or different, and are eachindependently selected from deuterium, halogen group, cyano, haloalkylwith 1 to 10 carbon atoms, alkyl with 1 to 10 carbon atoms, cycloalkylwith 3 to 15 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthiowith 1 to 4 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms,triarylsilyl with 18 to 24 carbon atoms, aryl with 6 to 12 carbon atoms,aralkyl with 7 to 13 carbon atoms, heteroaryl with 4 to 12 carbon atoms,and heteroaralkyl with 5 to 13 carbon atoms;

n represents the number of Q¹, which is selected from 0; and mrepresents the number of Q², which is selected from 0 or 1;

Het is substituted or unsubstituted nitrogen-containing heteroaryl with3 to 30 carbon atoms;

Ar₁ and Ar₂ are the same or different, and are each independentlyselected from hydrogen, substituted or unsubstituted alkyl with 1 to 20carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbonatoms, and substituted or unsubstituted heteroaryl with 3 to 30 carbonatoms;

the substituents in the L, the Het, Ar₁ and Ar₂ are the same ordifferent, and are each independently selected from deuterium, halogengroup, cyano, aryl with 6 to 25 carbon atoms, heteroaryl with 3 to 25carbon atoms, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10carbon atoms, cycloalkyl with 3 to 10 carbon atoms, alkoxy with 1 to 10carbon atoms, alkylthio with 1 to 10 carbon atoms, trialkylsilyl with 3to 12 carbon atoms, and triarylsilyl with 18 to 24 carbon atoms. In thepresent disclosure, “Het can be substituted or unsubstitutednitrogen-containing heteroaryl with 3 to 30 carbon atoms” means that Hetcan contain substituent group or can not contain substituent group. WhenHet contains substituent group, the substituent group in Het refers tosubstituent group except Ar₁ and Ar₂.

In the present disclosure, the ring A and the ring B are the same ordifferent, and are each independently selected from a benzene ring or afused aromatic ring with 10 to 14 ring-forming carbon atoms, and thefused aromatic ring can be a naphthalene ring, an anthracene ring or aphenanthrene ring.

Preferably, in the present disclosure, the ring A or the ring B isphenyl; and L is connected with phenyl.

The nitrogen-containing compound provided by the present disclosure hasa molecular structure in which heteroaryl is bonded to fused-ringadamantane fluorene. On one hand, the molecular structure can reduce anenergy level injection barrier, so that the working voltage of anorganic electroluminescent device is reduced, and the open-circuitvoltage of a photoelectric conversion device is improved. On the otherhand, the molecular structure has large molecular weight, molecularasymmetry is increased, the structure can be adjusted, the material isdifficult to crystallize or aggregate, and the material has longerservice life in an electronic element. Not only that, the molecularstructure has electron-rich characteristics, the polarity of the wholemolecule is enhanced, and directional arrangement of material moleculesis facilitated, so that injection and transport of electrons areenhanced. In addition, the fused ring structure can enhance the electronconductivity of an electron transport material, can improve the luminousefficiency of an organic electroluminescent device using thenitrogen-containing compound, and can improve the conversion efficiencyof a photoelectric conversion device using the nitrogen-containingcompound.

In one embodiment of the present disclosure, the structural formula ofthe nitrogen-containing compound as shown in the Formula 1 is selectedfrom the group consisting of the following Formulae 2 to 19:

In one embodiment of the present disclosure, the structural formula ofthe nitrogen-containing compound as shown in the Formula 1 is selectedfrom the group consisting of the following Formulae 20 to 28:

In the present disclosure, because adamantane is of a three-dimensionalstructure, in a compound structure diagram, due to different drawingangles, different plane shapes can be presented, cyclic structuresformed on cyclopentane are all adamantane, and the connection positionsare the same. For example, the following structures

are the same.

In the present disclosure, the adopted description modes “each . . . areindependently”, “ . . . are respectively and independently” and “ . . .are independently selected from” can be interchanged, and should beunderstood in a broad sense, which means that in different groups,specific options expressed between the same symbols do not influenceeach other, or in a same group, specific options expressed between thesame symbols do not influence each other. For example, the meaning of “

where each q is independently 0, 1, 2 or 3, each R″ is independentlyselected from hydrogen, deuterium, fluorine and chlorine” is as follows:Formula Q-1 represents that q substituents R″ exist on a benzene ring,each R″ can be the same or different, and options of each R″ do notinfluence each other; and Formula Q-2 represents that each benzene ringof biphenyl has q substituents R″, the number q of the substituents R″on the two benzene rings can be the same or different, each R″ can bethe same or different, and options of each R″ do not influence eachother.

In the present disclosure, the term such as “substituted orunsubstituted” means that a functional group described behind the termmay have or do not have a substituent (hereinafter, the substituent iscollectively referred to as Rc in order to facilitate description). Forexample, the “substituted or unsubstituted aryl” refers to aryl havingthe substituent Rc or unsubstituted aryl. The above substituent, namelyRc can, for example, be deuterium, halogen group, cyano, aryl with 6 to25 carbon atoms, heteroaryl with 3 to 25 carbon atoms, alkyl with 1 to10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, cycloalkyl with 3to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkylthio with 1to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, andtriarylsilyl with 18 to 24 carbon atoms. In the present disclosure, the“substituted” functional group can be substituted by one or two or moresubstituents in the Rc; when two substituents Rc are connected to a sameatom, the two substituents Rc can independently exist or are connectedwith each other to form a ring with the atom; and when two adjacentsubstituents Rc exist on the functional group, the two adjacentsubstituents Rc can independently exist or are fused with the functionalgroup connected with the two adjacent substituents Rc to form a ring.

In the present disclosure, the number of carbon atoms in the substitutedor unsubstituted functional group refers to the number of all carbonatoms. For example, if Ar₁ is selected from substituted aryl with 30carbon atoms, the number of all carbon atoms of the aryl and thesubstituents thereon are 30.

In the present disclosure, the number of carbon atoms of L, Ar₁, Ar₂ andHet refers to the number of all carbon atoms. For example, if L issubstituted arylene with 12 carbon atoms, the number of all carbon atomsof the arylene and the substituents thereon are 12. For example, if Ar₁is

the number of carbon atoms is 7; and if L is

the number of carbon atoms is 12.

In the present disclosure, aryl refers to an optional functional groupor substituent derived from an aromatic carbocyclic ring. The aryl maybe monocyclic aryl (e.g., phenyl) or polycyclic aryl, in other words,the aryl may be monocyclic aryl, fused aryl, which is formed by two ormore monocyclic aryl conjugatedly connected through carbon-carbon bonds,formed by a monocyclic aryl and fused aryl which are conjugatedlyconnected through a carbon-carbon bond, or formed by two or more fusedaryl conjugatedly connected through carbon-carbon bonds. That is, unlessotherwise noted, two or more aromatic groups conjugatedly connected bycarbon-carbon bonds can also be regarded as the aryl groups in thepresent disclosure. The fused aryl may, for example, contain bicyclicfused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthryl,fluorenyl, and anthryl), and the like. The aryl does not containheteroatoms such as B, N, O, S, P, Se and Si. For example, in thepresent disclosure, phenyl or the like is the aryl. Examples of the arylmay contain, but are not limited to, phenyl, naphthyl, fluorenyl,anthryl, phenanthryl, biphenyl, terphenyl, quaterphenyl, quinquephenyl,benzo[9,10]phenanthryl, pyrenyl, benzofluoranthenyl, chrysenyl, and thelike. In the present disclosure, the arylene involved is a divalentgroup formed by further loss of one hydrogen atom from aryl.

In the present disclosure, the fused aromatic ring refers to apolyaromatic ring formed by two or more aromatic rings or heteroaromaticrings which share ring edges, such as naphthalene, anthracene,phenanthrene and pyrene.

In the present disclosure, the substituted aryl refers to one or two ormore hydrogen atoms in the aryl being substituted by a group such as adeuterium atom, halogen group, —CN, aryl, heteroaryl, trialkylsilyl,alkyl, cycloalkyl, alkoxy, alkylthio and the like. Specific examples ofheteroaryl-substituted aryl contain, but are not limited to,dibenzofuranyl-substituted phenyl, dibenzothienyl-substituted phenyl,pyridyl-substituted phenyl, and the like. It should be understood thatthe number of carbon atoms in the substituted aryl refers to the totalnumber of carbon atoms of the aryl and substituents on the aryl, forexample, the substituted aryl with 18 carbon atoms means that the totalnumber of carbon atoms of the aryl and the substituents thereon are 18.

In the present disclosure, the arylene involved is a divalent groupformed by further loss of one hydrogen atom from aryl.

In the present disclosure, the heteroaryl refers to a monovalentaromatic ring containing at least one heteroatom in a ring or aderivative thereof, and the heteroatom can be at least one of B, O, N,P, Si, Se and S. The heteroaryl may be monocyclic heteroaryl orpolycyclic heteroaryl, in other words, the heteroaryl may be a singlearomatic ring system or a polycyclic systems formed by multiple aromaticrings conjugatedly connected through carbon-carbon bonds, where any oneof the aromatic ring system is an aromatic monocyclic ring or anaromatic fused ring. Exemplarily, the heteroaryl may contain thienyl,furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl,triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl,pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl,phenothiazinyl, phenoxazinyl, phthalazinyl, pyridinopyrimidyl,pyridinopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl,benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl,benzothienyl, dibenzothienyl, thienothienyl, benzofuryl,phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl,phenothiazinyl, silafluorenyl, dibenzofuryl and N-arylcarbazolyl (e.g.,N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl),N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, but is notlimited thereto. Among them, thienyl, furyl, phenanthrolinyl etc. areheteroaryl groups of a single aromatic ring system, and theN-arylcarbazolyl and N-heteroarylcarbazolyl are heteroaryl groups of amultiple aromatic ring systems conjugatedly connected throughcarbon-carbon bonds.

In the present disclosure, the nitrogen-containing heteroaryl refers toa monovalent aromatic ring containing at least one heteroatom in a ringor a derivative thereof, and the heteroatom can be at least one of B, O,N, P, Si, Se and S, and at least has one N.

In the present disclosure, the heteroarylene involved refers to adivalent group formed by further loss of one hydrogen atom fromheteroaryl.

In the present disclosure, the substituted heteroaryl refer to one ortwo or more hydrogen atoms in the heteroaryl being substituted by agroup such as a deuterium atom, halogen group, —CN, aryl, heteroaryl,trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio and the like.Specific examples of aryl-substituted heteroaryl contain but are notlimited to phenyl-substituted dibenzofuranyl, phenyl-substituteddibenzothienyl, phenyl-substituted pyridyl and the like. It should beunderstood that the number of carbon atoms of the substituted heteroarylrefers to the total number of carbon atoms of heteroaryl andsubstituents on the heteroaryl.

In the present disclosure, the alkyl with 1 to 20 carbon atoms can belinear alkyl or branched alkyl. Specifically, the alkyl with 1 to 20carbon atoms can be linear alkyl with 1 to 20 carbon atoms or branchedalkyl with 3 to 20 carbon atoms. The number of carbon atoms may, forexample, be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17,18, 19 or 20. Specific embodiments of the alkyl with 1 to 20 carbonatoms include but are not limited to methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, tert-butyl, n-amyl, isoamyl, neopentyl, cyclopentyl,n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyland the like.

In the present disclosure, the halogen group can be fluorine, chlorine,bromine or iodine.

In the present disclosure, an unpositioned connecting bond is a singlebond

extending from a ring system, which means that one end of the connectingbond can be connected with any position in the ring system through whichthe bond penetrates, and the other end of the connecting bond isconnected with the remaining part of a compound molecule.

For example, as shown in the following Formula (f), naphthyl representedby the Formula (f) is connected to other positions of a molecule throughtwo unpositioned connecting bonds penetrating a dicyclic ring, and itsmeaning includes any one possible connecting mode represented byFormulae (f-1) to (f-10).

For example, as shown in the following formula (X′), dibenzofuranylrepresented by the formula (X′) is connected with other positions of amolecule through one unpositioned connecting bond extending from themiddle of a benzene ring on one side, and its meaning includes any onepossible connecting mode represented by formulae (X′-1) to (X′-4).

In one specific embodiment of the present disclosure, the ring A and thering B are the same or different, and are each independently selectedfrom a benzene ring, a naphthalene ring, a phenanthrene ring and ananthracene ring, and the ring A and the ring B are not benzene rings atthe same time.

In one specific embodiment of the disclosure,

is selected from the group consisting of structures shown below:

where

represents a chemical bond used for connection with

in the above

structures, and

represents a chemical bond used for connection with

in the above structures.

In one specific embodiment of the present disclosure, in

n=1 and

is selected from the group consisting of structures shown below:

where,

represents a chemical bond used for connection with

in the above

structures, and

represents a chemical bond used for connection with

in the above structures.

In one specific embodiment of the present disclosure,

is selected from the group consisting of structures shown below:

where,

represents a chemical bond used for connection with

in the above

structures, and

represents a chemical bond used for connection with

in the above structures.

In one specific embodiment of the present disclosure, in

m=1 and

is selected from the group consisting of structures shown below:

where,

represents a chemical bond used for connection with

in the above

structures, and

represents a chemical bond used for connection with

in the above structures.

In one specific embodiment of the present disclosure, the Ar₁ and theAr₂ are the same or different, and are each independently selected fromhydrogen, substituted or unsubstituted alkyl with 1 to 10 carbon atoms,substituted or unsubstituted cycloalkyl with 3 to 10 carbon atoms,substituted or unsubstituted aryl with 6 to 24 carbon atoms, andsubstituted or unsubstituted heteroaryl with 5 to 24 carbon atoms.

Optionally, in the present disclosure, the Ar₁ and the Ar₂ are the sameor different, and are each independently selected from aryl with 6 to 21carbon atoms and substituted or unsubstituted heteroaryl with 5 to 20carbon atoms.

Preferably, in the present disclosure, the Ar₁ and the Ar₂ are the sameor different, and are each independently selected from aryl with 6 to 20carbon atoms and substituted or unsubstituted heteroaryl with 5 to 12carbon atoms.

In one specific embodiment of the present disclosure, the substituentsin Ar₁ and Ar₂ are the same or different, and are each independentlyselected from deuterium, halogen group, cyano, aryl with 6 to 20 carbonatoms, heteroaryl with 3 to 20 carbon atoms, alkyl with 1 to 5 carbonatoms, haloalkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 10carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4carbon atoms, trialkylsilyl with 3 to 7 carbon atoms, and triarylsilylwith 18 to 24 carbon atoms. Specifically, the substituents in Ar₁ andAr₂ are the same or different, and are each independently selected fromdeuterium, fluorine, cyano, methyl, ethyl, tert-butyl, phenyl, naphthyl,biphenyl, terphenyl, dimethylfluorenyl, N-phenylcarbazolyl,dibenzofuryl, dibenzothienyl, quinolyl, pyridyl, pyrimidyl,phenothiazinyl and phenoxazinyl.

In one specific embodiment of the present disclosure, Ar₁ and Ar₂ arethe same or different, and are each independently selected from hydrogenor the group consisting of groups as shown in i-1 to i-15 below:

where M₁ is selected from a single bond or

G₁ to G₅ and G₁′ to G₄′ are each independently selected from N, C orC(J₁), at least one of G₁ to G₅ is selected from N, and when two or moreof G₁ to G₅ are selected from C(J₁), any two J₁s are the same ordifferent;

G₆ to G₁₃ are each independently selected from N, C or C(J₂), and atleast one of G₆ to G₁₃ is selected from N; and when two or more of G₆ toG₁₃ are selected from C(J₂), any two J₂s are the same or different;

G₁₄ to G₂₃ are each independently selected from N, C or C(J₃), and atleast one of G₁₄ to G₂₃ is selected from N; and when two or more of G₁₄to G₂₃ are selected from C(J₃), any two J₂s are the same or different;

G₂₄ to G₃₃ are each independently selected from N, C or C(J₄), and atleast one of G₂₄ to G₃₃ is selected from N; and when two or more of G₂₄to G₃₃ are selected from C(J₄), any two J₃s are the same or different;

Z₁ is selected from hydrogen, deuterium, halogen group, cyano,trialkylsilyl with 3 to 12 carbon atoms, alkyl with 1 to 10 carbonatoms, haloalkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10carbon atoms, alkoxy with 1 to 10 carbon atoms, alkylthio with 1 to 10carbon atoms and triarylsilyl with 18 to 24 carbon atoms;

Z₂ to Z₉ and Z₂₁ are each independently selected from hydrogen,deuterium, halogen group, cyano, trialkylsilyl with 3 to 12 carbonatoms, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbonatoms, cycloalkyl with 3 to 10 carbon atoms, alkoxy with 1 to 10 carbonatoms, alkylthio with 1 to 10 carbon atoms, heteroaryl with 3 to 18carbon atoms and triarylsilyl with 18 to 24 carbon atoms;

Z₁₀ to Z₂₀ and J₁ to J₄ are each independently selected from hydrogen,deuterium, halogen group, cyano, trialkylsilyl with 3 to 12 carbonatoms, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbonatoms, cycloalkyl with 3 to 10 carbon atoms, alkoxy with 1 to 10 carbonatoms, alkylthio with 1 to 10 carbon atoms, aryl with 6 to 18 carbonatoms optionally substituted by one or more of deuterium, fluorine,chlorine and cyano, heteroaryl with 3 to 18 carbon atoms, andtriarylsilyl with 18 to 24 carbon atoms; in the present disclosure,“aryl with 6 to 18 carbon atoms optionally substituted by one or more ofdeuterium, fluorine, chlorine and cyano” means that the aryl can besubstituted by deuterium, fluorine, chlorine and cyano and also can notbe substituted by deuterium, fluorine, chlorine and cyano.

h₁ to h₂₁ are represented by h_(k), Z₁ to Z₂₁ are represented by Z_(k),k is a variable and represents any integer of 1 to 21, and h_(k)represents the number of substituents Z_(k); when k is selected from 5or 17, h_(k) is selected from 1, 2 or 3; when k is selected from 2, 7,8, 12, 15, 16, 18 or 21, h_(k) is selected from 1, 2, 3 or 4; when k isselected from 1, 3, 4, 6, 9 or 14, h_(k) is selected from 1, 2, 3, 4 or5; when k is 13, h_(k) is selected from 1, 2, 3, 4, 5 or 6; when k isselected from 10 or 19, h_(k) is selected from 1, 2, 3, 4, 5, 6 or 7;when k is 20, h_(k) is selected from 1, 2, 3, 4, 5, 6, 7 or 8; when k is11, h_(k) is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when h_(k)is greater than one, any two Z_(k)s are the same or different;

K₁ is selected from O, S, N(Z₂₂), C(Z₂₃Z₂₄) and Si(Z₂₈Z₂₉); where Z₂₂,Z₂₃, Z₂₄, Z₂₈ and Z₂₉ are each independently selected from aryl with 6to 18 carbon atoms, heteroaryl with 3 to 18 carbon atoms, alkyl with 1to 10 carbon atoms or cycloalkyl with 3 to 10 carbon atoms, or the Z₂₃and the Z₂₄ are connected with each other to form a saturated orunsaturated ring with 3 to 15 carbon atoms together with atoms to whichthey are jointly connected, or the Z₂₈ and the Z₂₉ are connected witheach other to form a saturated or unsaturated ring with 3 to 15 carbonatoms together with atoms to which they are jointly connected;

K₂ is selected from a single bond, O, S, N(Z₂₅), C(Z₂₆Z₂₇), andSi(Z₃₀Z₃₁); where Z₂₅, Z₂₆, Z₂₇, Z₃₀ and Z₃₁ are each independentlyselected from aryl with 6 to 18 carbon atoms, heteroaryl with 3 to 18carbon atoms, alkyl with 1 to 10 carbon atoms or cycloalkyl with 3 to 10carbon atoms, or the Z₂₆ and the Z₂₇ are connected with each other toform a saturated or unsaturated ring with 3 to 15 carbon atoms togetherwith atoms to which they are jointly connected, or the Z₃₀ and the Z₃₁are connected with each other to form a saturated or unsaturated ringwith 3 to 15 carbon atoms together with atoms to which they are jointlyconnected.

In one specific embodiment of the present disclosure, Ar₁ and Ar₂ arethe same or different, and are each independently selected from hydrogenor the group consisting of the following groups:

In one specific embodiment of the present disclosure, Ar₁ and Ar₂ arethe same or different, and are each independently selected from hydrogenor the group consisting of the following groups:

In one specific embodiment of the present disclosure, the Het isunsubstituted nitrogen-containing heteroaryl with 3 to 25 carbon atoms.

Preferably, in the present disclosure, the Het is unsubstitutednitrogen-containing heteroaryl with 3 to 20 carbon atoms.

In one specific embodiment of the present disclosure, in the Formula 1,

is selected from the following groups:

where,

represents a chemical bond.

In one specific embodiment of the present disclosure,

is selected from the group consisting of the following groups:

Wherein, in the above groups containing X₁, X₂ and X₃, the X₁, the X₂and the X₃ are independently selected from CH or N, and at least one ofthe X₁, the X₂ and the X₃ is N.

In the present disclosure, L is selected from a single bond, substitutedor unsubstituted arylene with 6 to 20 carbon atoms, and substituted orunsubstituted heteroarylene with 3 to 20 carbon atoms.

Preferably, L is selected from a single bond, substituted orunsubstituted arylene with 6 to 18 carbon atoms, and substituted orunsubstituted heteroarylene with 3 to 18 carbon atoms; furtherpreferably, L is selected from a single bond, substituted orunsubstituted arylene with 6 to 15 carbon atoms, and substituted orunsubstituted heteroarylene with 5 to 12 carbon atoms.

In the present disclosure, L is selected from a single bond, substitutedor unsubstituted phenylene, substituted or unsubstituted naphthylene,substituted or unsubstituted biphenylene, substituted or unsubstitutedterphenylene, substituted or unsubstituted fluorenylidene, substitutedor unsubstituted dibenzothienylidene, substituted or unsubstituteddibenzofurylidene, and substituted or unsubstituted pyridylidene.

In the present disclosure, the substituent in L is selected fromdeuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, arylwith 6 to 12 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms.Specifically, in the present disclosure, the substituent in the L isselected from deuterium, fluorine, cyano, methyl, ethyl, tert-butyl,phenyl, naphthyl, biphenyl and terphenyl.

In the present disclosure, L is selected from a single bond or the groupconsisting of groups as shown in j-1 to j-14:

where M₂ is selected from a single bond or

and

represents a chemical bond;

Q₁ to Q₅ and Q′₁ to Q′₅ are each independently selected from N or C(J₅),and at least one of Q₁ to Q₅ is selected from N; and when two or more ofQ₁ to Q₅ are selected from C(J₅), any two J₅s are the same or different,and when two or more of Q′₁ to Q′₄ are selected from C(J₅), any two J₅sare the same or different;

Q₆ to Q₁₃ are each independently selected from N, C or C(J₆), and atleast one of Q₆ to Q₁₃ is selected from N; and when two or more of Q₆ toQ₁₃ are selected from C(J₆), any two LS are the same or different;

Q₁₄ to Q₂₃ are each independently selected from N, C or C(J₇), and atleast one of Q₁₄ to Q₂₃ is selected from N; and when two or more of Q₁₄to Q₂₃ are selected from C(J₇), any two J₇s are the same or different;

Q₂₄ to Q₃₃ are each independently selected from N, C or C(J₈), and atleast one of Q₂₄ to Q₃₃ is selected from N; and when two or more of Q₂₄to Q₃₃ are selected from C(J₈), any two J₈s are the same or different;

E₁ to E₁₄ and J₅ to J₈ are each independently selected from hydrogen,deuterium, halogen group, cyano, heteroaryl with 3 to 20 carbon atoms,aryl with 6 to 20 carbon atoms optionally substituted by one or more ofdeuterium, fluorine, chlorine and cyano, trialkylsilyl with 3 to 12carbon atoms, arylsilyl with 8 to 12 carbon atoms, alkyl with 1 to 10carbon atoms, haloalkyl with 1 to 10 carbon atoms, alkenyl with 2 to 6carbon atoms, alkynyl with 2 to 6 carbon atoms, cycloalkyl with 3 to 10carbon atoms, heterocycloalkyl with 2 to 10 carbon atoms, cycloalkenylwith 5 to 10 carbon atoms, heterocycloalkenyl with 4 to 10 carbon atoms,alkoxy with 1 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms,aryloxy with 6 to 18 carbon atoms, arylthio with 6 to 18 carbon atoms,phosphinyloxy with 6 to 18 carbon atoms and triarylsilyl with 18 to 24carbon atoms; in the present disclosure, “aryl with 6 to 20 carbon atomsoptionally substituted by one or more of deuterium, fluorine, chlorineand cyano” means that the aryl can be substituted by deuterium,fluorine, chlorine and cyano and also can not be substituted bydeuterium, fluorine, chlorine and cyano.

e₁ to e₁₄ are represented by er, E₁ to E₁₄ are represented by E_(r), ris a variable and represents any integer of 1 to 14, and er representsthe number of substituents E_(r); when r is selected from 1, 2, 3, 4, 5,6, 9, 13 or 14, er is selected from 1, 2, 3 or 4; when r is selectedfrom 7 or 11, er is selected from 1, 2, 3, 4, 5 or 6; when r is 12, eris selected from 1, 2, 3, 4, 5, 6 or 7; when r is selected from 8 or 10,er is selected from 1, 2, 3, 4, 5, 6, 7 or 8; and when the er is greaterthan one, any two Ers are the same or different;

K₃ is selected from O, S, Se, N(E₁₅), C(E₁₆E₁₇) and Si(E₁₈E₁₉); whereE₁₅, E₁₆, E₁₇, E₁₈ and E₁₉ are each independently selected from arylwith 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, alkylwith 1 to 10 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynylwith 2 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms,heterocycloalkyl with 2 to 10 carbon atoms, cycloalkenyl with 5 to 10carbon atoms, and heterocloalkenyl with 4 to 10 carbon atoms; or E₁₆ andE₁₇ are connected with each other to form a saturated or unsaturatedring with 3 to 15 carbon atoms together with atoms to which they arejointly connected, or E₁₈ and E₁₉ are connected with each other to forma saturated or unsaturated ring with 3 to 15 carbon atoms together withatoms to which they are jointly connected;

K₄ is selected from a single bond, O, S, Se, N(E₂₀), C(E₂₁E₂₂) andSi(E₂₃E₂₄); where E₂₀-E₂₄ are each independently selected from aryl with6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, alkyl with 1to 10 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, heterocycloalkylwith 2 to 10 carbon atoms, cycloalkenyl with 5 to 10 carbon atoms, andheterocloalkenyl with 4 to 10 carbon atoms; or E₂₁ and E₂₂ are connectedwith each other to form a saturated or unsaturated ring with 3 to 15carbon atoms together with atoms to which they are jointly connected, orE₂₃ and E₂₄ are connected with each other to form a saturated orunsaturated ring with 3 to 15 carbon atoms together with atoms to whichthey are jointly connected.

In one specific embodiment of the present disclosure, L is selected froma single bond or the group consisting of the following groups:

In one specific embodiment of the present disclosure, L is selected froma single bond or the group consisting of the following groups:

In one specific embodiment of the disclosure, the nitrogen-containingcompound is selected from the group consisting of the followingcompounds:

A synthesis method of the nitrogen-containing compound provided by thepresent disclosure is not specially limited, and those skilled in theart can determine a proper synthesis method according to thenitrogen-containing compound provided by the present disclosure incombination with a preparation method provided in the synthesisexamples. In other words, the synthesis examples of the presentdisclosure exemplarily provide a preparation method of thenitrogen-containing compound, and the adopted raw materials can beobtained commercially or by a method well known in the field. All thenitrogen-containing compounds provided by the present disclosure can beobtained by those skilled in the art according to these exemplarypreparation methods, and all specific preparation methods for preparingthe nitrogen-containing compound are no longer detailed, which shouldnot be understood by those skilled in the art as limiting the presentdisclosure.

In a second aspect, the present disclosure provides an electronicelement, comprising an anode, a cathode which are arranged oppositely tothe anode, and a functional layer arranged between the anode and thecathode; the functional layer contains the nitrogen-containing compounddescribed in the first aspect of the present disclosure.

In one specific embodiment, the functional layer comprises an electrontransport layer, and the electron transport layer contains thenitrogen-containing compound. The electron transport layer can becomposed of the nitrogen-containing compound provided by the presentdisclosure, and can also be composed of the nitrogen-containing compoundprovided by the present disclosure and other materials. The electrontransport layer can be one or two or more.

In one specific embodiment, the functional layer comprises a holeblocking layer, and the hole blocking layer contains thenitrogen-containing compound.

In one specific embodiment, the electronic element is an organicelectroluminescent device or a photoelectric conversion device.

In one specific embodiment, the electronic element is an organicelectroluminescent device, such as a blue light device or a green lightdevice.

In one specific embodiment, the electronic element may be an organicelectroluminescent device. As shown in FIG. 1 , the organicelectroluminescent device can comprise an anode 100, a hole injectionlayer 310, a hole transport layer 321, an electron blocking layer 322,an organic light-emitting layer 330 as an energy conversion layer, ahole blocking layer 341, an electron transport layer 340, an electroninjection layer 350 and a cathode 200 which are sequentially stacked.

Optionally, the anode 100 contains the following anode materials.Preferably, it is a material having a large work function thatfacilitate hole injection into the functional layer. Specific examplesof the anode materials comprise metals such as nickel, platinum,vanadium, chromium, copper, zinc, and gold, or an alloy thereof; metaloxides such as zinc oxide, indium oxide, indium tin oxide (ITO) andindium zinc oxide (IZO); combined metals and oxides, such as ZnO:Al orSnO₂:Sb; or a conductive polymer such as poly(3-methylthiophene),poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, andpolyaniline, but are not limited thereto. It is preferable to include atransparent electrode containing indium tin oxide (ITO) as the anode.

Optionally, the hole transport layer 321 and the electron blocking layer322 respectively contain one or more hole transport materials, and thehole transport materials can be selected from a carbazole polymer,carbazole connected triarylamine compounds or other types of compounds,which are not specially limited in the present disclosure. For example,the hole transport layer 321 may be composed of a compound NPB or acompound HT-01, and the electron blocking layer 322 may contain acompound EB-01 or EB-02.

Optionally, the organic light-emitting layer 330 can be composed of asingle light-emitting material, and can also contain a host material anda doping material. Optionally, the organic light-emitting layer 330 iscomposed of a host material and a doping material, holes injected intothe organic light-emitting layer 330 and electrons injected into theorganic light-emitting layer 330 can be recombined in the organiclight-emitting layer 330 to form excitons, the excitons transfer energyto the host material, the host material transfers energy to the dopingmaterial, which in turn enables the doping material to emit light.

The host material of the organic light-emitting layer 330 can be a metalchelated compound, a distyryl derivative, an aromatic amine derivative,a dibenzofuran derivative or other types of materials, which is notspecially limited in the present disclosure. In one embodiment of thepresent disclosure, the host material of the organic light-emittinglayer 330 can be BH-01 or a mixed host material, such as a GH-n1 andGH-n2 mixed host material.

The doping material of the organic light-emitting layer 330 can be acompound having a condensed aryl ring or a derivative thereof, acompound with a heteroaryl ring or a derivative thereof, an aromaticamine derivative or other materials, which is not specially limited inthe present disclosure. In one embodiment of the present disclosure, thedoping material of the organic light-emitting layer 330 may be BD-01 orIr(ppy)₃.

The electron transport layer 340 can be of a single-layer structure or amulti-layer structure and can contain one or more electron transportmaterials, and the electron transport materials can be selected from butare not limited to a benzimidazole derivative, an oxadiazole derivative,a quinoxaline derivative or other electron transport materials. In oneembodiment of the present disclosure, the electron transport layermaterial contains the nitrogen-containing compound provided in thepresent disclosure.

In the present disclosure, the specific structures of compounds such asEB-01, EB-02, BH-01, BD-01, GH-n1, GH-n2, ET-01 and the like are shownin the following examples, which will not be repeated here.

In the present disclosure, the cathode 200 may contain a cathodematerial, which is a material with a small work function thatcontributes to electron injection into the functional layer. Specificembodiments of the cathode material contain, but are not limited to,metals such as magnesium, calcium, sodium, potassium, titanium, indium,yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or analloy thereof; or a plurality of layers of materials such as LiF/Al,Liq/Al, LiO₂/Al, LiF/Ca, LiF/Al, and BaF₂/Ca. It is preferable toinclude a metal electrode containing magnesium and silver as thecathode.

Optionally, as shown in FIG. 1 , a hole injection layer 310 is arrangedbetween the anode 100 and the hole transport layer 321 to enhance theability of injecting holes into the hole transport layer 321. The holeinjection layer 310 may be selected from a benzidine derivative, astarburst arylamine compound, a phthalocyanine derivative or othermaterials, which is not specially limited in the present disclosure. Forexample, the hole injection layer 310 may be composed of F4-TCNQ.

Optionally, as shown in FIG. 1 , an electron injection layer 350 isarranged between the cathode 200 and the electron transport layer 340 toenhance the ability of injecting electrons into the electron transportlayer 340. The electron injection layer 350 may include an inorganicmaterial such as an alkali metal sulfide, and an alkali metal halide, ormay contain a complex of an alkali metal and an organic substance. Forexample, the electron injection layer 350 may contain Yb.

According to another embodiment, the electronic element may be aphotoelectric conversion device. As shown in FIG. 3 , the photoelectricconversion device can comprise an anode 100 and a cathode 200 which areoppositely arranged, and a functional layer 300 arranged between theanode 100 and the cathode 200; the functional layer 300 contains thenitrogen-containing compound provided in the present disclosure.

According to one specific embodiment, as shown in FIG. 3 , thephotoelectric conversion device can comprise an anode 100, a holetransport layer 321, a photoelectric conversion layer 360, an electrontransport layer 340 and a cathode 200 which are sequentially stacked.

Optionally, the photoelectric conversion device can be a solar cell,especially an organic thin-film solar cell. For example, in one exampleof the present disclosure, the solar cell can include an anode, a holetransport layer, a photoelectric conversion layer, an electron transportlayer and a cathode which are sequentially stacked, and thephotoelectric conversion layer contains the nitrogen-containing compoundprovided of the present disclosure.

In a third aspect, the present disclosure provides an electronic device,which includes the electronic element in the second aspect of thepresent disclosure.

According to one embodiment, as shown in FIG. 2 , the electronic deviceis a first electronic device 400, and the first electronic device 400comprises the organic electroluminescent device. The first electronicdevice 400 may be a display device, a lighting device, an opticalcommunication device or other types of electronic devices, for example,it may include, but is not limited to, a computer screen, a mobile phonescreen, a television, electronic paper, an emergency lighting lamp, anoptical module and the like.

According to another embodiment, as shown in FIG. 4 , the electronicdevice is a second electronic device 500, and the second electronicdevice 500 comprises the photoelectric conversion device. The secondelectronic device 500 may, for example, be a solar power plant, a lightdetector, a fingerprint identification device, a light module, a CCDcamera, or other types of electronic devices.

The synthesis method of the nitrogen-containing compound of the presentdisclosure is specifically described below in combination with thesynthesis examples, but the present disclosure is not limited thereby.

The compounds in the synthesis method which are not mentioned in thepresent disclosure are all commercially available raw material products.

An ICP-7700 mass spectrometer and an M5000 elemental analyzer are usedfor analysis and detection of intermediates and compounds in the presentdisclosure.

SYNTHETIC EXAMPLES

Y-1 (100 g, 398.5 mmol), Z-1 (96.3 g, 398.5 mmol),tetrakis(triphenylphosphine)palladium (2.3 g, 1.9 mmol), potassiumcarbonate (110.2 g, 797.1 mmol), tetrabutylammonium chloride (0.55 g,1.9 mmol), toluene (800 mL), ethanol (400 mL) and deionized water (200mL) were added into a three-necked flask, under the protection ofnitrogen, the reaction solution was raised to 78° C., and stirred for 6h; the resulting reaction solution was cooled to room temperature,toluene (300 mL) was added for extraction, organic phases were combined,dried withr anhydrous magnesium sulfate, and filtered to obtain afiltrate, and the filtrate was concentrated under reduced pressure toobtain a crude product; and the obtained crude product was purified bysilica gel column chromatography using n-heptane as a mobile phase, andthen purified through recrystallization by using adichloromethane/n-heptane system (a volume ratio of 1:3) to obtain SM-1(112.8 g, yield: 77%).

Y-2 (32.9 g, 272.2 mmol), Z-2 (100 g, 272.2 mmol),tetrakis(triphenylphosphine)palladium (9.4 g, 8.2 mmol), potassiumcarbonate (112.8 g, 816.5 mmol), tetrabutylammonium chloride (0.75 g,2.72 mmol), toluene (800 mL), ethanol (400 mL) and deionized water (200mL) were added into a three-necked flask, under the protection ofnitrogen, the reaction solution was raised to 78° C., and stirred for 8h; the resulting reaction solution was cooled to room temperature,toluene (300 mL) was added for extraction, organic phases were combined,dried with anhydrous magnesium sulfate, and filtered to obtain afiltrate, and the filtrate was concentrated under reduced pressure toobtain a crude product; and the obtained crude product was purifiedthrough recrystallization by using a dichloromethane/n-heptane system (avolume ratio of 1:3) to obtain SM-2 (64.8 g, yield: 75%).

Y-3 (100 g, 350.5 mmol), Z-3 (71.5 g, 350.5 mmol),tetrakis(triphenylphosphine)palladium (12.1 g, 10.5 mmol), potassiumcarbonate (145.3 g, 1051.5 mmol), tetrabutylammonium chloride (0.97 g,3.5 mmol), toluene (800 mL), ethanol (400 mL) and deionized water (200mL) were added into a three-necked flask, under the protection ofnitrogen, the reaction solution was raised to 78° C., and stirred for 6h; the resulting reaction solution was cooled to room temperature,toluene (300 mL) was added for extraction, organic phases were combined,dried with anhydrous magnesium sulfate, and filtered to obtain afiltrate, and the filtrate was concentrated under reduced pressure toobtain a crude product; and the obtained crude product was purified bysilica gel column chromatography using n-heptane as a mobile phase, andthen purified through recrystallization by using adichloromethane/n-heptane system (a volume ratio of 1:3) to obtain SM-3(82.4 g, yield: 74%).

In a dry round-bottom flask, a magnesium ribbon (22.9, 944.5 mmol) anddiethyl ether (250 mL) were placed under the protection of nitrogen, and250 mg of iodine was added. Then, SMA-1 (100 g, 314.4 mmol) dissolvedinto diethyl ether (500 mL) was slowly dropped into the flask. Afterdropped, the temperature was raised to 35° C. and the reaction solutionwas stirred for 3 h; the resulting reaction solution was cooled to 0°C., the solution of adamantanone (37.8 g, 252 mmol) dissolved intodiethyl ether (500 mL) was slowly added dropwise thereto. After thedropwise addition, the temperature was raised to 35° C., and stirred for6 h; the resulting reaction solution was cooled to room temperature, and5% hydrochloric acid was added into the reaction solution until a pH<7,and the stirring was performed for 1 h, diethyl ether (500 mL) was addedinto the reaction solution for extraction, organic phases were combined,dried with anhydrous magnesium sulfate, and filtered, and the solventwas removed under reduced pressure; and the obtained crude product waspurified by silica gel column chromatography using n-heptane as a mobilephase to obtain a solid intermediate IM-A-1 (97.8 g, yield: 80%).

An intermediate IM-A-X was synthesized by adopting a method which is thesame as intermediate IM-A-1, except that SMA-X (50 g) was used forreplacing SMA-1 to prepare the intermediate IM-A-X, X can be 2 to 12,and the prepared intermediate IM-A-X is shown in Table 1.

TABLE 1 Mass Yield SMA-X Intermediate IM-A-X (g) (%)

48.3 79

47.1 77

46.5 76

47.1 77

45.9 75

45.3 74

47.7 78

47.1 77

46.6 78

47.7 78

47.1 77

The intermediate IM-A-1 (40 g, 102.8 mmol) and trifluoroacetic acid (400mL) were added into a reaction flask, stirring was started, then themixture was gradually raised to 80° C., a reflux reaction was carriedout for 12 h, after the reaction was completed, the resulting reactionsolution was poured into water (in a volume ratio of 1:20), stirring wasperformed for 30 min, filtering was performed, drip washing wasperformed with water (in a volume ratio of 1:2), drip washing wasperformed with ethanol (in a volume ratio of 1:2), and the obtainedcrude product was recrystallized with dichloromethane and n-heptane in avolume ratio of 1:2 to obtain an intermediate IM-B-1 (30.5 g, yield:80%).

An intermediate IM-B-X was synthesized by adopting a method which is thesame as the method for synthesizing the intermediate IM-B-1, except thatthe intermediate IM-B-X and an intermediate IM-B-X-0 were prepared byreplacing the intermediate IM-A-1 with the intermediate IM-A-X, X can be2 to 12, and the prepared intermediate IM-B-X is shown in Table 2.

TABLE 2 Mass Yield Intermediate IM-A-X Intermediate IM-B-X (g) (%)

17.1 41

11.7 39

24.4 81

24.9 83

11.4 38

11.7 39

25.3 84

24.9 83

11.4 38

11.1 37

24.6 82

31.4 82

25.3 84

24.9 83

The intermediate IM-B-1 (15 g, 40.4 mmol), bis(pinacolato)diboron (10.3g, 40.4 mmol), tris(dibenzylideneacetone)dipalladium (0.74 g, 0.81mmol), 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (0.19 g, 0.40mmol), potassium acetate (7.9 g, 80.8 mmol) and 1,4-dioxane (150 mL)were added into a reaction flask, under the protection of nitrogen, thereaction solution was raised to 110° C., and stirred under heating andrefluxing for 5 h. The resulting reaction solution was cooled to roomtemperature, and extracted by using dichloromethane and water, anorganic layer was dried with anhydrous magnesium sulfate, and filtered,the obtained filtrate was allowed to pass through a short silica gelcolumn, the solvent was removed under reduced pressure, and the obtainedcrude product was purified through recrystallization by using adichloromethane/n-heptane (a volume ratio of 1:3) system to obtain anintermediate IM-C-1 (14.0 g, yield: 75%).

An intermediate IM-C-X was synthesized by adopting a method which is thesame as the method for synthesizing the intermediate IM-C-1, except thatthe intermediate IM-B-X was used for replacing the intermediate IM-B-1to prepare the intermediate IM-C-X and an intermediate IM-C-X-0, X canbe 1 to 12, and the prepared intermediate IM-C-X is shown in Table 3.

TABLE 3 Mass Yield Intermediate IM-B-X Intermediate IM-C-X (g) (%)

IM- B-2

IM- C-2 14.0 75

IM- B-2- 0

IM- C-2- 0 13.6 73

IM- B-3

IM- C-3 13.3 71

IM- B-4

IM- C-4 13.8 74

IM- B-5

IM- C-5 13.6 73

IM- B-5- 0

IM- C-5- 0 14.2 76

IM- B-6

IM- C-6 13.6 73

IM- B-7

IM- C-7 13.8 74

IM- B-8

IM- C-8 14.0 75

IM- B-8- 0

IM- C-8- 0 13.8 74

IM- B-9

IM- C-9 14.2 76

IM- B-10

IM- C-10 13.6 75

IM- B-11

IM- C-11 13.6 73

IM- B-12

IM- C-12 13.8 74

The intermediate IM-C-1 (5.00 g, 10.8 mmol), a raw material 1 (CAS.NO.:182918-13-4) (5.46 g, 13.0 mmol), palladium acetate (0.12 g, 0.54 mmol),2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (0.26 g, 0.54 mmol),potassium carbonate (3.29 g, 23.8 mmol), toluene (40 mL), ethanol (20mL) and water (10 mL) were added into a reaction flask, under theprotection of nitrogen, the reaction solution was raised to 78° C., andstirred under heating and refluxing for 5 h. The resulting reactionsolution was cooled to room temperature, and extracted by usingdichloromethane and water, an organic layer was dried with anhydrousmagnesium sulfate, and filtered, the obtained filtrate was allowed topass through a short silica gel column, the solvent was removed underreduced pressure, and the obtained crude product was purified throughrecrystallization by using a dichloromethane/n-heptane (a volume ratioof 1:3) system to obtain a compound A-1 (6.24 g, yield: 80%). Massspectrum: m/z=720.3[M+H]⁺.

A compound A-X was synthesized by adopting a method which is the same asthe method for synthesizing the compound A-1, except that theintermediate IM-C-X was used for replacing the intermediate IM-C-1, anda raw material M was used for replacing the raw material 1 (182918-13-4)to prepare the compound A-X or B-139. The prepared compounds A-X andB-139 are as shown in Table 4.

TABLE 4 Intermediate IM-C-X Raw material M

IM-C-2

IM-C-1

IM-C-3

IM-C-4

IM-C-5

IM-C-5

IM-C-6

IM-C-7

IM-C-8

IM-C-10

IM-C-11

IM-C-12

Mass (g)/yield (%)/mass Compound A-X spectrum

A-2 5.50/79/644.3

A-18 5.86/78/695.3

A-5 5.93/79/694.3

A-14 5.85/78/694.3

A-10 5.43/78/644.3

A-119 5.48/77/658.3

A-137 4.38/75/541.3

A-136 4.26/73/541.3

A-147 4.52/72/581.3

A-95 5.50/76/669.3

A-121 4.74/77/569.3

A-126 5.77/78/684.3

A-143 5.26/73/667.3

A-146 4.77/74/597.3

B-139 5.15/70/681.3

A-117 5.92/76/720.3

A-251 5.34/75/658.3

A-279 6.15/76/748.3

A-201 5.13/76/624.3

A-259 5.46/75/674.3

A-290 6.25/74/780.3

A-315 4.69/78/618.3

A-245 5.40/77/649.3

A-151 5.22/75/644.3

The intermediate IM-C-1 (5.00 g, 10.8 mmol), SM-b (187275-76-9) (4.66 g,13.0 mmol), palladium acetate (0.12 g, 0.54 mmol),2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (0.26 g, 0.54 mmol),potassium carbonate (3.29 g, 23.8 mmol), toluene (40 mL), ethanol (20mL) and water (10 mL) were added into a reaction flask, the reactionsolution was heated to 78° C. under the protection of nitrogen, andstirred under heating and refluxing for 5 h. The resulting reactionsolution was cooled to room temperature, and extracted by usingdichloromethane and water, an organic layer was dried with anhydrousmagnesium sulfate, and filtered, the obtained filtrate was allowed topass through a short silica gel column, the solvent was removed underreduced pressure, and the obtained crude product was purified throughrecrystallization by using a dichloromethane/n-heptane (a volume ratioof 1:3) system to obtain an intermediate IM-D-1 (4.91 g, yield: 80%).

An intermediate IM-D-X was synthesized by adopting a method which is thesame as the synthesis method of the intermediate IM-D-1, except that theintermediate IM-C-X was used for replacing the intermediate IM-C-1, andSM-X was used for replacing SM-b to prepare the intermediate IM-D-X.Where X can be 2 to 19, and the prepared intermediate IM-D-X is shown inTable 5.

TABLE 5 Intermediate IM-C-X SM-X

IM-C-2

IM-C-2-0

IM-C-3

IM-C-1

IM-C-4

IM-C-5

IM-C-5-0

IM-C-6

IM-C-7

IM-C-8

IM-C-8-0

IM-C-9

IM-C-10

IM-C-11

IM-C-12

Mass (g)/yield Intermediate IM-D-X (%)

IM-D-2 4.14/78

IM-D-3 4.66/76

IM-D-4 4.72/77

IM-D-5 4.56/78

IM-D-6 4.39/75

IM-D-7 4.14/78

IM-D-10 4.50/77

IM-D-11 4.44/76

IM-D-8 4.60/75

IM-D-9 4.78/78

IM-D-14 4.77/76

IM-D-13 4.60/75

IM-D-16 4.09/77

IM-D-15 4.60/75

IM-D-12 4.14/78

IM-D-17 4.06/77

IM-D-18 4.78/78

IM-D-19 4.66/76

The intermediate IM-D-1 (4.00 g, 7.05 mmol) and tetrahydrofuran (40 mL)were added into a reaction flask, and the temperature was cooled to −78°C. in a nitrogen environment, n-butyllithium (0.52 g, 8.10 mmol) wasdropwise added into the reaction solution. After the addition, thetemperature of the reaction solution was maintained for 1 h, a rawmaterial 2 (1.88 g, 7.05 mmol) was dropwise added, the temperature wascontinued to maintain for 1 h, and the temperature was naturally raisedto room temperature 12 h, so that a solid was separated out from thereaction solution, filtering was performed by using a Buchner funnel toobtain a crude product, and the obtained crude product was purifiedthrough recrystallization by using a toluene (150 mL) system to obtain acompound B-11 (3.24, yield: 64%). Mass spectrum: m/z=720.3[M+H]⁺.

A compound B-Y was synthesized by adopting a method which is the same asthe method for synthesizing the compound B-11, except that theintermediate IM-D-X was used for replacing the intermediate IM-D-1, anda raw material SMX was used for replacing the raw material 2 (CAS.NO.:3842-55-5) to prepare the compound B-Y. The prepared compound Y is shownin Table 6.

TABLE 6 Intermediate IM-D-X SMX

IM- D-6

IM- D-2

IM- D-3

IM- D-4

IM- D-5

IM- D-7

IM- D-10

IM- D-11

IM- D-8

IM- D-9

IM- D-14

IM- D-13

IM- D-16

IM- D-15

IM- D-12

IM- D-17

IM- D-18

IM- D-19

Mass (g)/yield (%)/mass Compound B-Y spectrum

B- 25 3.69/65/770.3

B- 2 4.13/66/770.3

B- 9 3.64/65/796.4

B- 13 3.41/65/741.3

B- 23 3.38/66/694.3

B- 35 3.80/65/720.3

B- 50 3.15/64/667.3

B- 56 3.58/63/770.3

B- 44 3.24/64/720.3

B- 46 3.38/65/738.3

B- 91 3.39/66/748.3

B- 72 3.29/65/720.3

B- 102 4.42/66/824.3

B- 100 3.90/67/826.3

B- 66 3.16/65/720.3

B- 130 3.27/64/694.3

B- 98 3.19/63/720.3

B- 65 3.50/64/776.4

NMR data of partial compounds is as shown in Table 7

TABLE 7 Compound NMR data Compound ¹H NMR (400 Hz, CD₂Cl₂): 9.37 (s,1H), 8.79(d, 4H), A-1 8.49 (d, 1H), 7.91-7.85 (m, 6H), 7.79-7.73 (m,2H), 7.68 (d, 1H), 7.64-7.60 (m, 9H), 7.52-7.49 (m, 3H), 3.17 (d, 2H),3.00 (d, 2H), 2.36 (s, 1H), 2.27 (s, 1H), 2.07 (s, 2H), 1.94 (t, 4H),1.74 (s, 2H). Compound ¹H NMR (400 Hz, CD₂Cl₂): 9.16 (s, 1H), 9.08 (d,4H), B-11 8.94 (d, 1H), 8.51 (s, 1H), 8.31-8.26 (m, 2H), 8.17-7.87 (m,17H), 7.66 (d, 1H), 3.15 (d, 2H), 3.02 (d, 2H), 2.38 (s, 1H), 2.26 (s,1H), 2.10 (s, 2H), 1.96 (t, 4H), 1.75 (s, 2H).

An organic electroluminescent device was manufactured by adopting thefollowing method:

Example 1 Blue Organic Electroluminescent Device

An anode was prepared by the following processes: an ITO substrate witha thickness of 1500 Å (manufactured by Corning) was cut into a size of40 mm×40 mm×0.7 mm to be prepared into an experimental substrate with acathode, an anode and an insulating layer pattern by adopting aphotoetching process, and surface treatment was performed by utilizingultraviolet ozone and O₂:N₂ plasma to increase the work function of theanode (the experiment substrate), and remove scum.

F4-TCNQ was vacuum-evaporated on the experiment substrate (the anode) toform a hole injection layer (HIL) having a thickness of 100 Å, and HT-01was evaporated on the hole injection layer to form a hole transportlayer having a thickness of 1000 Å.

EB-01 was vacuum-evaporated on the hole transport layer to form anelectron blocking layer with a thickness of 100 Å.

BH-01 and BD-01 were co-evaporated on the electron blocking layer in aratio of 98%:2% to form an organic light-emitting layer (EML) with athickness of 220 Å.

A compound ET-01 was evaporated on the organic light-emitting layer toform a hole blocking layer (HBL) having a thickness of 50 Å.

A compound A-1 and LiQ were mixed at a weight ratio of 1:1 andevaporated on the hole blocking layer to form an electron transportlayer (ETL) having a thickness of 300 Å.

Yb was evaporated on the electron transport layer to form an electroninjection layer (EIL) having a thickness of 10 Å, and then magnesium(Mg) and silver (Ag) were mixed at an evaporation rate of 1:10 andvacuum-evaporated on the electron injection layer to form a cathodehaving a thickness of 140 Å.

In addition, CP-1 with a thickness of 630 Å was evaporated on thecathode to form an organic capping layer (CPL), so that themanufacturing of the organic light-emitting device was completed, andthe structure is shown in FIG. 1 .

Examples 2 to 26

An organic electroluminescent device was manufactured by adopting thesame method that in Example 1, except that when the electron transportlayer was manufactured, the nitrogen-containing compound A-1 wasrespectively replaced by the nitrogen-containing compounds shown inTable 9.

Example 27

An organic electroluminescent device was manufactured by adopting thesame method that in Example 1, except that when the hole blocking layerwas formed, the compound ET-01 was replaced by a nitrogen-containingcompound B-11 of the present disclosure, and when the electron transportlayer was formed, the nitrogen-containing compound A-1 of the presentdisclosure was replaced by the compound ET-01.

Examples 28 to 48

An organic electroluminescent device was manufactured by adopting thesame method that in Example 27, except that when the hole blocking layerwas formed, the nitrogen-containing compound B-11 was respectivelyreplaced by the nitrogen-containing compounds shown in Table 9.

Example 49

An organic electroluminescent device was manufactured by adopting thesame method that in Example 1, except that when the hole blocking layerwas formed, the compound ET-01 was replaced by the nitrogen-containingcompound A-1 of the present disclosure, and when the electron transportlayer was formed, the nitrogen-containing compound A-1 was replaced by anitrogen-containing compound B-9.

Example 50

An organic electroluminescent device was manufactured by adopting thesame method that in Example 1, except that when the hole blocking layerwas formed, the compound ET-01 was replaced by a nitrogen-containingcompound A-5 of the present disclosure, and when the electron transportlayer was formed, the nitrogen-containing compound A-1 was replaced by anitrogen-containing compound B-13.

Example 51

An organic electroluminescent device was manufactured by adopting thesame method that in Example 1, except that when the hole blocking layerwas formed, the compound ET-01 was replaced by a nitrogen-containingcompound A-14 of the present disclosure, and when the electron transportlayer was formed, the nitrogen-containing compound A-1 was replaced by anitrogen-containing compound B-23.

Example 52

An organic electroluminescent device was manufactured by adopting thesame method that in Example 1, except that when the hole blocking layerwas formed, the compound ET-01 was replaced by a nitrogen-containingcompound A-10 of the present disclosure, and when the electron transportlayer was formed, the nitrogen-containing compound A-1 was replaced by anitrogen-containing compound B-56.

Example 53

An organic electroluminescent device was manufactured by adopting thesame method that in Example 1, except that when the hole blocking layerwas formed, the compound ET-01 was replaced by a nitrogen-containingcompound A-201 of the present disclosure, and when the electrontransport layer was formed, the nitrogen-containing compound A-1 wasreplaced by a nitrogen-containing compound B-102.

Comparative Example 1

An organic electroluminescent device was manufactured by adopting thesame method that in Example 1, except that when the electron transportlayer was manufactured, the nitrogen-containing compound A-1 wasreplaced by a compound A.

Comparative Example 2

An organic electroluminescent device was manufactured by adopting thesame method that in Example 1, except that when the electron transportlayer was manufactured, the nitrogen-containing compound A-1 wasreplaced by a compound B.

Comparative Example 3

An organic electroluminescent device was manufactured by adopting thesame method that in Example 1, except that when the electron transportlayer was manufactured, the nitrogen-containing compound A-1 wasreplaced by Alq3.

Comparative Example 4

An organic electroluminescent device was manufactured by adopting thesame method that in Example 27, except that when the hole blocking layerwas manufactured, the nitrogen-containing compound B-11 was replaced bythe compound A.

Comparative Example 5

An organic electroluminescent device was manufactured by adopting thesame method that in Example 27, except that when the hole blocking layerwas manufactured, the nitrogen-containing compound B-11 was replaced bythe compound B.

Comparative Example 6

An organic electroluminescent device was manufactured by adopting thesame method that in Example 27, except that when the hole blocking layerwas manufactured, the nitrogen-containing compound B-11 was replaced byAlq3.

The structures of the compounds adopted in the comparative examples andthe compound ET-01 are shown in Table 8.

TABLE 8

F4-TCNQ

HT-01

EB-01

BH-01

BD-01

ET-01

LiQ

CP-01

Compound A

Compound B

Alq3

The photoelectric properties of the manufactured organicelectroluminescent device were analyzed under the condition of 10A/cm²and 20 mA/cm², and the results are shown in the following Table 9:

TABLE 9 T95 (hrs)@20mA/ HBL ETL Volt (V) Cd/A Im/W CIE-x CIE-y EQE % cm²Example 1 ET-01 Compound 3.88 6.91 5.59 0.14 0.05 14.21 213 A-1 Example2 ET-01 Compound 3.89 6.61 5.34 0.14 0.05 13.61 211 A-2 Example 3 ET-01Compound 3.94 6.78 5.41 0.14 0.05 13.95 192 A-18 Example 4 ET-01Compound 3.89 6.92 5.59 0.14 0.05 14.23 211 A-5 Example 5 ET-01 Compound3.92 6.84 5.51 0.14 0.05 14.07 193 A-14 Example 6 ET-01 Compound 3.826.84 5.63 0.14 0.05 14.07 198 A-10 Example 7 ET-01 Compound 3.90 6.695.39 0.14 0.05 13.76 190 A-119 Example 8 ET-01 Compound 3.92 6.67 5.350.14 0.05 13.72 207 A-137 Example 9 ET-01 Compound 3.81 6.89 5.68 0.140.05 14.17 187 A-95 Example 10 ET-01 Compound 3.82 6.59 5.42 0.14 0.0513.56 190 A-121 Example 11 ET-01 Compound 3.92 6.57 5.27 0.14 0.05 13.51195 A-126 Example 12 ET-01 Compound 3.83 6.73 5.52 0.14 0.05 13.78 204A-117 Example 13 ET-01 Compound 3.87 6.56 5.33 0.14 0.05 13.49 209 A-251Example 14 ET-01 Compound 3.91 6.79 5.46 0.14 0.05 13.97 197 A-279Example 15 ET-01 Compound 3.86 6.88 5.62 0.14 0.05 14.15 199 A-201Example 16 ET-01 Compound 3.83 6.62 5.43 0.14 0.05 13.62 215 A-259Example 17 ET-01 Compound 3.92 6.78 5.43 0.14 0.05 13.95 183 A-290Example 18 ET-01 Compound 3.98 6.33 5.00 0.14 0.05 13.02 188 B-9 Example19 ET-01 Compound 3.99 6.27 4.94 0.14 0.05 12.90 182 B-13 Example 20ET-01 Compound 4.02 6.30 4.92 0.14 0.05 12.96 182 B-23 Example 21 ET-01Compound 4.00 6.24 4.90 0.14 0.05 12.84 187 B-56 Example 22 ET-01Compound 4.01 6.24 4.89 0.14 0.05 12.84 207 B-102 Example 23 ET-01Compound 4.01 6.77 4.94 0.14 0.05 13.93 202 A-136 Example 24 ET-01Compound 3.97 6.73 4.94 0.14 0.05 13.83 192 A-147 Example 25 ET-01Compound 3.95 6.77 4.94 0.14 0.05 13.84 197 A-143 Example 26 ET-01Compound 3.99 6.67 4.94 0.14 0.05 13.60 195 A-146 Example 27 CompoundET-01 3.88 6.68 5.41 0.14 0.05 13.74 184 B-11 Example 28 Compound ET-013.84 6.56 5.37 0.14 0.05 13.49 183 B-25 Example 29 Compound ET-01 3.896.59 5.32 0.14 0.05 13.56 186 B-2 Example 30 Compound ET-01 3.92 6.825.47 0.14 0.05 14.03 193 B-9 Example 31 Compound ET-01 3.89 6.75 5.450.14 0.05 13.88 192 B-13 Example 32 Compound ET-01 3.88 6.68 5.41 0.140.05 13.74 199 B-23 Example 33 Compound ET-01 3.89 6.60 5.33 0.14 0.0513.58 199 B-35 Example 34 Compound ET-01 3.91 6.58 5.29 0.14 0.05 13.54184 B-50 Example 35 Compound ET-01 3.88 6.80 5.51 0.14 0.05 13.99 198B-56 Example 36 Compound ET-01 3.86 6.61 5.38 0.14 0.05 13.60 194 B-44Example 37 Compound ET-01 3.88 6.69 5.42 0.14 0.05 13.76 189 B-46Example 38 Compound ET-01 3.87 6.69 5.43 0.14 0.05 13.76 192 B-91Example 39 Compound ET-01 3.87 6.60 5.36 0.14 0.05 13.58 200 B-72Example 40 Compound ET-01 3.85 6.84 5.58 0.14 0.05 14.07 182 B-102Example 41 Compound ET-01 3.87 6.67 5.41 0.14 0.05 13.72 193 B-100Example 42 Compound ET-01 3.90 6.76 5.45 0.14 0.05 13.91 194 B-66Example 43 Compound ET-01 3.95 6.58 5.05 0.14 0.05 13.42 193 B-139Example 44 Compound ET-01 3.97 6.31 4.99 0.14 0.05 12.98 177 A-1 Example45 Compound ET-01 4.03 6.34 4.94 0.14 0.05 13.04 175 A-5 Example 46Compound ET-01 3.98 6.42 5.07 0.14 0.05 13.21 176 A-14 Example 47Compound ET-01 4.05 6.26 4.86 0.14 0.05 12.88 176 A-10 Example 48Compound ET-01 3.99 6.24 4.91 0.14 0.05 12.84 179 A-201 Example 49Compound Compound 3.79 6.53 5.52 0.14 0.05 13.43 194 A-1 B-9 Example 50Compound Compound 3.81 6.56 5.33 0.14 0.05 13.49 189 A-5 B-13 Example 51Compound Compound 3.82 6.49 5.42 0.14 0.05 13.35 190 A-14 B-23 Example52 Compound Compound 3.78 6.57 5.27 0.14 0.05 13.51 195 A-10 B-56Example 53 Compound Compound 3.76 6.49 5.68 0.14 0.05 13.35 187 A-201B-102 Comparative ET-01 Compound 4.24 5.85 4.41 0.14 0.05 12.03 144Example 1 A Comparative ET-01 Compound 4.17 5.72 4.31 0.14 0.05 11.77118 Example 2 B Comparative ET-01 Alq3 4.39 5.33 3.98 0.14 0.05 10.96 96Example 3 Comparative Compound ET-01 4.26 5.83 4.31 0.14 0.05 11.99 143Example 4 A Comparative Compound ET-01 4.27 5.72 4.16 0.14 0.05 11.75122 Example 5 B Comparative Alq3 ET-01 4.37 5.22 3.89 0.14 0.05 10.74 93Example 6

From Table 9, it can be seen that when the compound provided of thepresent disclosure is used as an electron transport layer material inExamples 1 to 26, compared with Comparative Examples 1 to 3, the currentefficiency and the service life of the device are obviously improved,the voltage is at least reduced by 0.15 V, the luminous efficiency is atleast improved by 6.72%, the external quantum efficiency is at leastimproved by 6.73%, and the service life is at least improved by 26.39%.Compared with the devices using the compounds in which L is not a singlebond in Examples 18 to 22, the devices using the compounds in which L isa single bond in Examples 1 to 17 are more excellent in variousproperties.

When the compound provided of the present disclosure is used as a holeblocking layer material in Examples 27 to 48, compared with ComparativeExamples 4 to 6, the current efficiency and the service life of thedevice are obviously improved, the voltage is at least reduced by 0.21V, the luminous efficiency is at least improved by 7.03%, the externalquantum efficiency is at least improved by 7.09%, and the service lifeis at least improved by 22.4%. Compared with the devices using thecompounds in which L is a single bond in Examples 44 to 48, the devicesusing the compounds in which L is not a single bond in Examples 27 to 43are more excellent in various properties.

When the compounds provided of the present disclosure are simultaneouslycombined to serve as a hole blocking layer and an electron transportlayer in Examples 49 to 53, compared with Comparative Examples 1 to 6,the voltage is obviously reduced and is at least reduced by 0.35 V, theluminous efficiency is at least improved by 10.94%, the external quantumefficiency is at least improved by 10.97%, and the service life is atleast improved by 29.86%.

Example 54: Green Organic Electroluminescent Device

An anode was prepared by the following processes: a substrate with anITO thickness of 1500 Å(manufactured by Corning) was cut into a size of40 mm×40 mm×0.7 mm to be prepared into an experimental substrate with acathode, an anode and an insulating layer pattern by adopting aphotoetching process, and surface treatment was performed by utilizingultraviolet ozone and O₂:N₂ plasma to increase the work function of theanode (the experiment substrate), and remove scum.

F4-TCNQ was vacuum-evaporated on the experiment substrate (the anode) toform a hole injection layer (HIL) having a thickness of 100 Å, and HT-01was evaporated on the hole injection layer to form a hole transportlayer having a thickness of 1000 Å.

EB-02 was vacuum-evaporated on the hole transport layer to form anelectron blocking layer with a thickness of 400 Å.

GH-n1, GH-n2 and Ir(ppy)₃ were co-evaporated on the electron blockinglayer in a ratio of 50%:45%:5% (an evaporation rate) to form a greenorganic light-emitting layer (EML) with a thickness of 400 Å.

A compound ET-01 was evaporated on the organic light-emitting layer toform a hole blocking layer (HBL) having a thickness of 50 Å.

A compound A-1 and LiQ were mixed at a weight ratio of 1:1 andevaporated on the hole blocking layer to form an electron transportlayer (ETL) having a thickness of 300 Å.

Yb was evaporated on the electron transport layer to form an electroninjection layer (EIL) having a thickness of 10 Å, and then magnesium(Mg) and silver (Ag) were mixed at an evaporation rate of 1:10 andvacuum-evaporated on the electron injection layer to form a cathodehaving a thickness of 140 Å.

In addition, CP-1 with a thickness of 650 Å was evaporated on thecathode to form an organic capping layer (CPL), so that themanufacturing of the organic light-emitting device was completed, andthe structure is shown in FIG. 1 .

Examples 55 to 62

An organic electroluminescent device was manufactured by adopting thesame method that in Example 54, except that when the electron transportlayer was manufactured, the nitrogen-containing compound A-1 wasrespectively replaced by the nitrogen-containing compounds shown inTable 11.

Example 63

An organic electroluminescent device was manufactured by adopting thesame method that in Example 54, except that when the hole blocking layerwas formed, the compound ET-01 was replaced by the nitrogen-containingcompound B-9 of the present disclosure, and when the electron transportlayer was formed, the nitrogen-containing compound A-1 of the presentdisclosure was replaced by the compound ET-01.

Examples 64 to 71

An organic electroluminescent device was manufactured by adopting thesame method that in Example 63, except that when the hole blocking layerwas formed, the nitrogen-containing compound B-9 was respectivelyreplaced by the nitrogen-containing compounds shown in Table 11.

Comparative Example 7

An organic electroluminescent device was manufactured by adopting thesame method that in Example 54, except that when the electron transportlayer was manufactured, the nitrogen-containing compound A-1 wasreplaced by a compound A.

Comparative Example 8

An organic electroluminescent device was manufactured by adopting thesame method that in Example 54, except that when the electron transportlayer was manufactured, the nitrogen-containing compound A-1 wasreplaced by a compound B.

Comparative Example 9

An organic electroluminescent device was manufactured by adopting thesame method that in Example 54, except that when the electron transportlayer was manufactured, the nitrogen-containing compound A-1 wasreplaced by Alq3.

Comparative Example 10

An organic electroluminescent device was manufactured by adopting thesame method that in Example 63, except that when the hole blocking layerwas manufactured, the nitrogen-containing compound B-9 was replaced bythe compound A.

Comparative Example 11

An organic electroluminescent device was manufactured by adopting thesame method that in Example 63, except that when the hole blocking layerwas manufactured, the nitrogen-containing compound B-9 was replaced bythe compound B.

Comparative Example 12

An organic electroluminescent device was manufactured by adopting thesame method that in Example 63, except that when the hole blocking layerwas manufactured, the nitrogen-containing compound B-9 was replaced byAlq3.

The structural formula of each used material is shown in the followingTable 10:

TABLE 10

F4-TCNQ

HT-01

EB-02

Ir(ppy)₃

ET-01

LiQ

CP-01

GH-n1

GH-n2

Compound A

Compound B

Alq3

The performance of the manufactured organic electroluminescent devicewas analyzed under the condition of 20 mA/cm², and the result is shownin the following Table 11:

TABLE 11 Performance test result of organic electroluminescent deviceT95 (hrs)@20mA/ HBL ETL Volt (V) Cd/A Im/W CIE-x CIE-y EQE % cm² Example54 ET-01 Compound 3.89 86.45 69.82 0.22 0.73 21.61 358 A-1 Example 55ET-01 Compound 3.87 86.82 70.48 0.22 0.73 21.71 324 A-5 Example 56 ET-01Compound 3.91 83.85 67.37 0.22 0.73 20.96 375 A-14 Example 57 ET-01Compound 3.94 88.36 70.45 0.22 0.73 22.09 358 A-10 Example 58 ET-01Compound 3.90 87.24 70.27 0.22 0.73 21.81 333 A-95 Example 59 ET-01Compound 3.91 84.07 67.55 0.22 0.73 21.02 356 A-201 Example 60 ET-01Compound 3.95 76.31 60.69 0.22 0.73 19.08 289 A-151 Example 61 ET-01Compound 3.97 75.19 59.50 0.22 0.73 18.80 292 A-245 Example 62 ET-01Compound 3.95 74.13 58.96 0.22 0.73 18.53 262 A-315 Example 63 CompoundET-01 3.85 83.99 68.53 0.22 0.73 21.00 354 B-9 Example 64 Compound ET-013.85 86.54 70.61 0.22 0.73 21.64 331 B-11 Example 65 Compound ET-01 3.9084.56 68.11 0.22 0.73 21.14 375 B-13 Example 66 Compound ET-01 3.9586.74 68.99 0.22 0.73 21.69 372 B-56 Example 67 Compound ET-01 3.8986.76 70.07 0.22 0.73 21.69 362 B-66 Example 68 Compound ET-01 3.9284.56 67.77 0.22 0.73 21.14 371 B-102 Example 69 Compound ET-01 3.9875.91 59.92 0.22 0.73 18.98 288 B-65 Example 70 Compound ET-01 3.9674.52 59.12 0.22 0.73 18.63 293 B-98 Example 71 Compound ET-01 3.9773.97 58.53 0.22 0.73 18.49 260 B-130 Comparative ET-01 Compound 4.0860.92 46.91 0.22 0.73 15.23 201 Example 7 A Comparative ET-01 Compound4.11 62.69 47.92 0.22 0.73 15.67 182 Example 8 B Comparative ET-01 Alq34.07 64.75 49.98 0.22 0.73 16.19 192 Example 9 Comparative CompoundET-01 4.07 65.25 50.36 0.22 0.73 16.31 197 Example 10 A ComparativeCompound ET-01 4.05 62.41 48.41 0.22 0.73 15.60 180 Example 11 BComparative Alq3 ET-01 4.11 63.13 48.25 0.22 0.73 15.78 186 Example 12

From Table 11, it can be seen that when the compound provided of thepresent disclosure is used as an electron transport layer material inExamples 54 to 62, compared with Comparative Examples 7 to 9, thecurrent efficiency and the service life of the device are obviouslyimproved, the voltage is at least reduced by 0.10 V, the luminousefficiency is at least improved by 14.5%, the external quantumefficiency is at least improved by 14.5%, and the service life is atleast improved by 30.3%.

When the compound provided of the present disclosure is used as a holeblocking layer material in Examples 63 to 71, compared with ComparativeExamples 10 to 12, the current efficiency and the service life of thedevice are obviously improved, the voltage is at least reduced by 0.07V, the luminous efficiency is at least improved by 13.4%, the externalquantum efficiency is at least improved by 13.4%, and the service lifeis at least improved by 32.0%.

Therefore, when the novel compound provided by the present disclosure isused for manufacting the organic electroluminescent device, the drivingvoltage of the device can be effectively reduced, and meanwhile, theservice life of the device is improved.

The preferable embodiments of the present disclosure are described indetail above n combination with the drawings, however, the presentdisclosure is not limited to the specific details in the aboveembodiments, in the technical concept range of the present disclosure,the technical solution of the present disclosure can be subjected tovarious simple variations, and these simple variations all belong to theprotection range of the present disclosure.

In addition, it should be noted that all the specific technical featuresdescribed in the above specific embodiments can be combined in anyappropriate mode without contradiction, and in order to avoidunnecessary repetition, various possible combinations are not describedany more in the present disclosure.

In addition, various different embodiments of the present disclosure canalso be combined at will, and as long as the embodiments do not violatethe idea of the present disclosure, the embodiments also should beregarded as the contents disclosed by the present disclosure.

1. A nitrogen-containing compound, having a structural formula as shownin Formula 1:

wherein ring A and ring B are the same or different, and are eachindependently selected from a benzene ring and a naphthalene ring, andthe ring A and the ring B are not benzene rings at the same time; L isselected from a single bond, unsubstituted phenylene, unsubstitutednaphthylene, unsubstituted biphenylene, unsubstituteddibenzothienylidene, and unsubstituted dibenzofurylidene; L is connectedwith the ring A or the ring B; each Q′ and each Q² are the same ordifferent, and are each independently selected from deuterium, halogengroup, cyano, haloalkyl with 1 to 10 carbon atoms, alkyl with 1 to 10carbon atoms, cycloalkyl with 3 to 15 carbon atoms, alkoxy with 1 to 4carbon atoms, alkylthio with 1 to 4 carbon atoms, trialkylsilyl with 3to 12 carbon atoms, triarylsilyl with 18 to 24 carbon atoms, aryl with 6to 12 carbon atoms, aralkyl with 7 to 13 carbon atoms, heteroaryl with 4to 12 carbon atoms, and heteroaralkyl with 5 to 13 carbon atoms; nrepresents the number of Q′, which is selected from 0; and m representsthe number of Q², which is selected from 0;

is selected from the following groups:

wherein,

represents a chemical bond; Ar₁ and Ar₂ are the same or different, andare each independently selected from hydrogen, substituted orunsubstituted phenyl, substituted or unsubstituted naphthyl, substitutedor unsubstituted biphenyl, substituted or unsubstituted terphenyl,substituted or unsubstituted fluorenyl, substituted or unsubstitutedpyridyl, substituted or unsubstituted dibenzofuranyl, and substituted orunsubstituted dibenzothienyl; the substituents in Ar₁ and Ar₂ are thesame or different, and are each independently selected from deuterium,fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl,naphthyl and quinolinyl.
 2. (canceled)
 3. The nitrogen-containingcompound according to claim 1, wherein the nitrogen-containing compoundas shown in the Formula 1 is selected from the group consisting of thefollowing compounds:


4. (canceled)
 5. (canceled)
 6. The nitrogen-containing compoundaccording to claim 1, wherein

is selected from the group consisting of structures shown below:

wherein

represents a chemical bond used for connection with

in the above structures, and

represents a chemical bond used for connection with

in the above structures.
 7. (canceled)
 8. The nitrogen-containingcompound according to claim 1, wherein

is selected from the group consisting of structures shown below:

wherein,

represents a chemical bond used for connection with

in the above structures, and

represents a chemical bond used for connection with

in the above structures.
 9. (canceled)
 10. (canceled)
 11. (canceled) 12.(canceled)
 13. The nitrogen-containing compound according to claim 1,wherein Ar₁ and Ar₂ are the same or different, and are eachindependently selected from hydrogen or the group consisting of thefollowing groups:


14. (canceled)
 15. (canceled)
 16. (canceled)
 17. (canceled)
 18. Thenitrogen-containing compound according to claim 1, wherein L is selectedfrom a single bond or the group consisting of the following groups:


19. The nitrogen-containing compound according to claim 1, wherein thenitrogen-containing compound is selected from the group consisting ofthe following compounds:


20. An electronic element, comprising an anode, a cathode which arearranged oppositely to the anode, and a functional layer arrangedbetween the anode and the cathode; the functional layer contains thenitrogen-containing compound according to claim
 1. 21. The electronicelement according to claim 20, wherein the electronic element is anorganic electroluminescent device or a photoelectric conversion device.22. (canceled)
 23. The electronic element according to claim 20, whereinthe functional layer comprises an electron transport layer, and theelectron transport layer contains the nitrogen-containing compound. 24.The electronic element according to claim 20, wherein the functionallayer comprises a hole blocking layer, and the hole blocking layercontains the nitrogen-containing compound.
 25. The electronic elementaccording to claim 21, wherein the organic electroluminescent device isa blue light device or a green light device.